Upon the Jews' initial entrance into Israel, Moshe addresses
his father in law as follows: (Numbers, 10:29)

(29) "Moshe said to Chovav, son of Reuale the Midianite,
father in law of Moshe, 'we are traveling to the place, upon
which God said I will give it to you,...Go with us and there
will be done good to you, as God has spoken good for Israel.
(30) Chovav said to Moshe, 'I will not go, unto my land and my
birthplace I will go'. (31) Moshe said, 'please do not forsake
us in as much as you know our travels in the desert, and you
will be to us as eyes. (32) And when you go with us, that good
which God will do unto us, He will do unto you."

Why was Moshe addressing his father in law at this time?
Did Moshe sense in Chovav some hesitation to remain with the
people of Israel? What was Moshe's initial argument, and why
did he mention Chovav's role of being a navigator only in passage
31? This was not stated by Moshe in his initial argument. What
does Chovav's response about "unto my land and my birthplace
I will go" come toteach us? Why mention Chovav
as "son of Reuale the Midianite"? We already
know who he is.

From Moshe's first statement in passage 29, we understand
that Moshe desired Chovav to enjoy the best life, "Go
with us and there will be done good to you, as God has spoken
good for Israel." Chovav responds, "I will not
go, unto my land and my birthplace I will go". Moshe
understands from this response that Chovav's attachment to his
land and birthplace outweigh his wish to relocate to Israel,
receiving the good from God. (The passage itself in describing
Chovav states, " Chovav, son of Reuale the Midianite",
hinting at Chovav's attachment to his father and his land.)
Moshe then tries to use Chovav's own mode of operation to attract
him: Chovav was a leader in Midian. He also demonstrated leadership
by suggesting a system of judges in parshas Yisro (Yisro and
Chovav are the same according to commentators). It appears that
Moshe intended to attract Chovav to the ultimate good promised
by God, by also appealing to Chovav's own motivations displayed
in "unto my land and my birthplace I will go",....
"and you will be to us as eyes" was Moshe's
attempt to do so.

Moshe did not initially suggest that Chovav take on some
leadership role by being their eyes. Moshe wanted to attract
Chovav to the good life, based on the good life itself. When
Moshe saw this was not attractive enough, he sought to add a
motive for Chovav, so Moshe mentioned that he would be as eyes
to the nation, a leadership role. But Moshe being committed to
the truth, would not allow this to be the sole argument for Chovav's
attachment to Israel, This is why Moshe again adds - even in
his second argument - that Chovav will attain the good promised
by God. To Moshe, this must always be the motive for following
Judaism - it is the ultimate good. No other consideration replaces
this as an argument to follow Judaism.